Brad Pitt.Photo: Kurt Krieger/Corbis
As one of the most handsome and famous men on the planet,Brad Pitthas quite the A-list dating history.
The Oscar winner counts several Hollywood superstars as his exes, including former wivesAngelina JolieandJennifer Aniston, former fiancéeGwyneth Paltrowand ex-girlfriendsJuliette LewisandChristina Applegate.
Pitt himself has insisted that most rumors about his personal life as a whole are false, especially when it comes to his relationships. Hetold theNew York Times Magazinein December 2019, “I stopped reading all press about 2004. Not just reviews. I mean any magazine in the doctor’s office,” he said. “Because some of it would bounce around like a rat in the skull. It would stay there, and it would inform some of my decisions and choices in work, in life, and I didn’t find any of it helpful.”
“I don’t go out of my way to avoid it; I just don’t seek it out,” he explained. “I don’t know how many women they’ve said I’ve been dating the last two or three years, and none of it’s true.”
Ahead, is a complete look atBrad Pitt’s dating history, from his reported fling with singer Sinitta in the ’80s to his most recent connection with Ines de Ramon.
Sinitta
Ron Galella, Ltd./Ron Galella Collection ; Jon Furniss/WireImage
Pitt and singer Sinitta reportedly dated from 1986 to 1988. The British pop star told her castmates onI’m a Celebrity … Get Me Out Of Here!in 2011 (viaMarie Claire UK) that Pitt was “beautiful with the most amazing body,” adding, “I saw him for two years. He was fun, he was young and very sweet. Some ardent fan gave me a slap when I came out of a supermarket over that relationship.”
She added, “It was before he madeThelma & Louise,but even I saw that movie and thought, “Oh my God, what have I done?' "
Jill Schoelen
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Pitt dated actress Jill Schoelen in the late 1980s after they met on the set of the horror movieCutting Class.
E.G. Daily
In Pitt’sE! True Hollywood Story, voice actress Elizabeth “E.G.” Daily revealed that she had a rebound romance with the star after he and Schoelen split. Daily described Pitt as “deep-souled” and “super cute” and said they connected in various ways.
“I think he was really intense about his work,” Daily said. “When you saw him, it was more like seething in him underneath. What I could feel from him was a really strong, visceral drive towards something really big.”
After Daily and Pitt called it quits on their brief romance, they remained friends.
Robin Givens
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Pitt and Robin Givens were costars onHead of the Classand grew close when she and then-estranged husbandMike Tysonseparated. Tyson alleged in his memoirUndisputed Truththat he pulled into his and Givens' driveway and saw her in a car with Pitt; he also claimed to have caught the pair in bed while Tyson and Givens were still together.
In a2019 interview onWatch What Happens Live with Andy Cohen, Givens denied an affair with Pitt.
“Pulling up in the driveway, that part is true,” Givens said at the time. “I didn’t read the book, but I was told he says he caught us in bed, which never happened. Never, ever, ever happened.”
As for why she and Pitt were in the car together, Givens said, “We were coming from like a screening or something.”
Christina Applegate
During a"Plead the Fifth” segmentonWatch What Happens Live With Andy Cohenin 2015, Applegate wouldn’t reveal the identity of the mystery man, but did note that she and Pitt didn’t date after the incident — nor did she date the man for whom she left him.
Juliette Lewis
Pitt andJuliette Lewisdated from late 1989 to 1993 and the pair costarred inKaliforniaandToo Young to Die.
Two years after their breakup, PitttoldVanity Fairof Lewis, “I still love the woman. There’s some real genius there. I had a great time with her … It was one of the greatest relationships I’ve ever been in.” He added, “The problem is, we grow up with this vision that love conquers all, and that’s just not so, is it?”
Though they remain friendly and each look back on the time fondly, Lewis isn’t too keen on being asked about her megastar ex.
In 2014, Lewis told PEOPLE that most press about her when she was younger was “usually aboutBrad Pittor drug addiction, which hasn’t been me since I was 22. I’m 40. I quit all my bulls— at 22. There is growth. Get out of the past.”
Jitka Pohlodek
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Pitt brought model Jitka Pohlodek as his date to the premiere ofLegends of the Fallin November 1994, but neither has spoken publicly about their brief romance. However, Pohlodek did latershare one glimpseinto her connection with the actor, telling PEOPLE in 2000, “The man glows.”
Gwyneth Paltrow
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Pitt metGwyneth Paltrowwhen she played his wife in the 1995 thrillerSe7en. Pitt called Paltrow his “angel” and the “love of [his] life” in his1996 Golden Globes acceptance speechfor Best Supporting Actor in12 Monkeys, and the pair got engaged that December. However, they split in June 1997 before ever making it down the aisle, and the Goop founder later recalled that her father, Bruce Paltrow, was particularly devastated because he adored Pitt.
Gwyneth and Pitt remained close, however, with Pitttelling her in a June 2022 conversation, “It’s lovely to have you as a friend now.”
Paltrowlooked back on their romanceduring an appearance on a May 2023 episode of theCall Her Daddypodcast.
The actress said it was “major, major love at first sight” when they met on the set ofSeven, adding, “It was crazy.”
She also recalled Pitt proposing. “One night we were on the balcony of this house we were renting in this little town in Argentina,” she said. “I wish I remembered exactly what he said, but he proposed, it was fantastic, I was thrilled. We had talked about it, but I was surprised in the moment, I remember that. I must have been 24.”
Jennifer Aniston
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Pitt metJennifer Anistonin 1998. He proposed to theFriendsstar in 1999, and the couple married in Malibu on July 29, 2000. The wedding featured some 200 guests, 50,000 flowers, four bands, a gospel choir and fireworks. “Jennifer looked beautiful,” her father,Days of Our Livesactor John Aniston told PEOPLE after escorting his daughter down the aisle. “It was a spectacular wedding.”
In January 2005, Pitt and Aniston shocked the world when they announced their split.
“They broke up, and they did it because they had serious issues,” a sourcetold PEOPLEin 2018. “They’re not stupid. They remember why it didn’t work.”
In 2021, Anistonmade it clear in an interview with Howard Sternthat she and Pitt are “buddies” and “friends.”
Angelina Jolie
Angelina Jolie and Brad Pitt in 2012.Pascal Le Segretain/Getty
Jolie and Pitt met while filmingMr. & Mrs. Smithin 2003, while he and Aniston were still married. Jolierecalled toVoguein 2007 that she and Pitt worked well together, though they didn’t become romantic right away.
“Because of the film, we ended up being brought together to do all these crazy things, and I think we found this strange friendship and partnership that kind of just suddenly happened,” she said. “I think a few months in I realized, ‘God, I can’t wait to get to work.’ … Anything we had to do with each other, we just found a lot of joy in it together and a lot of real teamwork. We just became kind of a pair.”
About Pitt’s marriage to Aniston, Jolie noted, “I didn’t know much about exactly where Brad was in his personal life. But it was clear he was with his best friend, someone he loves and respects.” She added, “It took until, really, the end of the shoot for us, I think, to realize that it might mean something more than we’d earlier allowed ourselves to believe. And both knowing that the reality of that was a big thing, something that was going to take a lot of serious consideration.”
In May 2006, Pitt and Jolie welcomed daughter Shiloh Nouvel. That December, theymade their red carpet debutas a couple at the New York City premiere of Jolie’s filmThe Good Shepherd. The following year, theyadoptedtheir son Pax Thien from Vietnam.
By 2012, Pitt revealed that his and Jolie’s childrenurged them to get married, and a rep for the pairconfirmed their engagementthat April (with a ringestimatedto be worth a cool $1 million). Pitt and Jolie tied the knot on Aug. 23, 2014, at the chapel in their Château Miraval estate, with Jolie wearing a gown that her children decorated with their own art. The children even helped the couple write their own vows.
“It was important to us that the day was relaxed andfull of laughter,” the couple told PEOPLE at the time. “It was such a special day to share with our children and a very happy time for our family.”
During their 2014 honeymoon, Jolie and Pitt worked together onBy the Sea, released in fall 2015.
On Sept. 20, 2016, just over two years after their second wedding anniversary, Joliefiled for divorcefrom Pitt. A rep for Jolie said in a statement, “Angelina Jolie-Pitt has filed for dissolution of the marriage. This decision was made for the health of the family. She will not be commenting at this time, and asks that the family be given their privacy during this difficult time.”
It waslater revealedthat Jolie’s filing came shortly after analleged heated altercationon a private plane became physical. Pitt denied striking any of the couple’s children, and the Los Angeles Department of Child and Protective Servicesfound no evidence of abuse. The FBI also closed an investigation into the incident without filing charges against theFight Clubstar.
By April 2019, the estranged pair weredeclared legally single. However, Pitt and Jolie’scontentiousnegotiationsover custody and division of assets didn’t conclude until December 2024 when a judge officiallysigned off on their divorce.
The former couple’s legal battle regardingtheir wineryremains ongoing.
Neri Oxman
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“Ittook him a long time to date, but he is now,” a source told PEOPLE, noting howGeorgeandAmal Clooney’s relationship inspired Pitt. “He likes women who challenge him in every way, especially in the intellect department. Brad has seen how happy and different Amal has made his friend. It has given him something to think about.” However, that October, Oxmandenied ever dating the actor, but praised him as “the last of the Mohicans in post-Netflix Hollywood … He brings together the timely and the timeless, which is what cinema is all about.”
Nicole Poturalski
Daniele Venturelli/Daniele Venturelli/WireImage
Pitt dated modelNicole Poturalskiin the summer of 2020, though the pair knew each other for at least a year before romance rumors came to light. A witness told PEOPLE that Pitt and Poturalski were spotted together at a 2019 Berlin Film Festival party forOnce Upon a Time … In Hollywood, noting, “They were very flirty.”
In August 2020, Pitt and Poturalski werespotted at Château Miravalin France, where a source said they were “enjoying each other’s company while traveling.” An industry insider also told PEOPLE that Poturalski was a good match for Pitt, saying, “I like her a lot. She has spunk. She’s smart. If she’s dating Brad, good for her. Good for him.”
However, just two months later, a source revealed to PEOPLE that Pitt and Poturalskiwere never serious, explaining, “Brad hasn’t seen Nicole since August. It was never a relationship. They saw each other a few times and that’s it. You can’t call it a split, because they were never together in the first place. It was a casual fling and that’s it.” Still, another source told PEOPLE in January 2022 that Pitt “still keeps in touch” with the model.
Emily Ratajkowski
Emily Ratajkowski.Gotham/FilmMagic
Pitt was linked to modelEmily Ratajkowskiin late September 2022 following hersplit from estranged husbandSebastian Bear-McClard. A source told PEOPLE that the pair are “spending a lot of time together,” though “friends aren’t sure if it’s serious,” and the two don’t “appear to be ‘dating’ formally.”
By the following month, multiple insiders were able to give a clearer picture of thecasual romance. A source close to Ratajkowski said the model is not looking to jump into a serious romance. “It’s the perfect timing right now. There is nothing likeBrad Pittcheering you up,” the insider said. “She wants to get to know him better.”
Another source says Ratajkowski “has the vibes that Brad likes. She’s bright and articulate.” She’s also a fellow art lover like Pitt, the insider added.
“They have a lot to talk about and always have a great time when they hang out,” a third source said. “There is an attraction, but nothing serious is going on. They have had a few dates and stay in touch when they don’t see each other.”
Ines de Ramon
Pascal Le Segretain/Getty
Pitt and de Ramon werefirst spotted together at a Bono concertin Los Angeles on Nov. 13, 2022. This occurred roughly two months after news broke thatde Ramon and husband Paul Wesley had quietly separatedin early 2022.
Later in November, PEOPLE spoke to a source close to de Ramon, who confirmed that the pair had been dating “for a few months.” The source added that they “met through a mutual friend” and Pitt is “really into” de Ramon.
A few days later, De Ramon and Pittspent his 59th birthday together. Photographers captured the casually dressed couple arriving at Pace — an Italian restaurant in Hollywood.
“Brad had abirthday party dinner with Ines and friendson Saturday night. Guests brought gifts and the group shared a lot of Italian food. Brad even got a birthday treat with a candle and the group sang happy birthday,” a source told PEOPLE.
“He was in the best mood,” the source added. “He sat next to Ines. They were very cute and flirty. You could tell that she makes him happy.”
In February 2024, PEOPLE learned thatde Ramon had moved into Pitt’s Los Angeles home.
“Things have been amazing since they moved in together,” an insider shared in July 2024. “It’s more of aserious relationshipthan just dating. Brad loves so many things about her. She’s great for him.”
Pitt and de Ramon eventually made theirred carpet debutin September 2024 at theWolfspremiere during the Venice Film Festival.
source: people.com
